Synthesis of rhodamine B-benzenesulfonamide conjugates and their inhibitory activity against human α- and bacterial/fungal β-carbonic anhydrases.

Abstract

A series of fluorescent sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors were obtained by attaching rhodamine B moieties to the scaffold of benzenesulfonamides. The new compounds have been investigated for the inhibition of 12 human α-CA isoforms (hCA I-hCA XIV), three bacterial and one fungal β-class enzymes from the pathogens Mycobacterium tuberculosis and Candida albicans. All types of inhibitory activities have been detected, with several compounds showing low nanomolar inhibition against the transmembrane isoforms hCA IX, XII (cancer-associated) and XIV. The β-CAs were inhibited in the micromolar range by these compounds which may have applications for the imaging of hypoxic tumors or bacteria due to their fluorescent moieties.

• Authors: Marouan Rami, Alessio Innocenti, Jean-Louis Montero, Andrea Scozzafava, Jean-Yves Winum, Claudiu T Supuran
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 21 Issue 18 Pg. 5210-3 (Sep 15 2011) ISSN: 1464-3405 [Electronic] England
• PMID: 21821413 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2011 Elsevier Ltd. All rights reserved.

Chemical References

• Carbonic Anhydrase Inhibitors
• Rhodamines
• Sulfonamides
• Carbonic Anhydrases
• rhodamine B

Topics

• Candida albicans (enzymology)
• Carbonic Anhydrase Inhibitors (chemical synthesis, chemistry, pharmacology)
• Carbonic Anhydrases (metabolism)
• Humans
• Molecular Structure
• Mycobacterium tuberculosis (enzymology)
• Rhodamines (chemistry)
• Stereoisomerism
• Structure-Activity Relationship
• Sulfonamides (chemistry)
• Benzenesulfonamides